GB1303724A - - Google Patents
Info
- Publication number
- GB1303724A GB1303724A GB2018270A GB2018270A GB1303724A GB 1303724 A GB1303724 A GB 1303724A GB 2018270 A GB2018270 A GB 2018270A GB 2018270 A GB2018270 A GB 2018270A GB 1303724 A GB1303724 A GB 1303724A
- Authority
- GB
- United Kingdom
- Prior art keywords
- wortmannin
- desacetoxy
- antibiotic
- formula
- fungistatic
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- GXVZXRZMWGYXMQ-UHFFFAOYSA-N 11-Desacetoxywortmannin Natural products C12CCC(=O)C1(C)CCC1=C2C(=O)C2=C3C(=CO2)C(=O)OC(COC)C13C GXVZXRZMWGYXMQ-UHFFFAOYSA-N 0.000 abstract 5
- GXVZXRZMWGYXMQ-DJOOALQISA-N 11-desacetoxywortmannin Chemical compound C1([C@]2(C)C3=C(C4=O)OC=C3C(=O)O[C@@H]2COC)=C4[C@@H]2CCC(=O)[C@@]2(C)CC1 GXVZXRZMWGYXMQ-DJOOALQISA-N 0.000 abstract 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract 3
- 230000003115 biocidal effect Effects 0.000 abstract 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- 230000001408 fungistatic effect Effects 0.000 abstract 2
- QDLHCMPXEPAAMD-QAIWCSMKSA-N wortmannin Chemical compound C1([C@]2(C)C3=C(C4=O)OC=C3C(=O)O[C@@H]2COC)=C4[C@@H]2CCC(=O)[C@@]2(C)C[C@H]1OC(C)=O QDLHCMPXEPAAMD-QAIWCSMKSA-N 0.000 abstract 2
- QDLHCMPXEPAAMD-UHFFFAOYSA-N wortmannin Natural products COCC1OC(=O)C2=COC(C3=O)=C2C1(C)C1=C3C2CCC(=O)C2(C)CC1OC(C)=O QDLHCMPXEPAAMD-UHFFFAOYSA-N 0.000 abstract 2
- 241000750600 Aspergillus janus Species 0.000 abstract 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 abstract 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- 206010061218 Inflammation Diseases 0.000 abstract 1
- 206010030113 Oedema Diseases 0.000 abstract 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract 1
- 241001136494 Talaromyces funiculosus Species 0.000 abstract 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 238000011097 chromatography purification Methods 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 238000000605 extraction Methods 0.000 abstract 1
- 239000000706 filtrate Substances 0.000 abstract 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 abstract 1
- 230000004054 inflammatory process Effects 0.000 abstract 1
- 230000002401 inhibitory effect Effects 0.000 abstract 1
- 238000006317 isomerization reaction Methods 0.000 abstract 1
- 239000000391 magnesium silicate Substances 0.000 abstract 1
- 229910052919 magnesium silicate Inorganic materials 0.000 abstract 1
- 235000019792 magnesium silicate Nutrition 0.000 abstract 1
- ZADYMNAVLSWLEQ-UHFFFAOYSA-N magnesium;oxygen(2-);silicon(4+) Chemical compound [O-2].[O-2].[O-2].[Mg+2].[Si+4] ZADYMNAVLSWLEQ-UHFFFAOYSA-N 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 239000012299 nitrogen atmosphere Substances 0.000 abstract 1
- 235000015097 nutrients Nutrition 0.000 abstract 1
- 239000002674 ointment Substances 0.000 abstract 1
- 150000007530 organic bases Chemical class 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000008024 pharmaceutical diluent Substances 0.000 abstract 1
- 239000000843 powder Substances 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000000741 silica gel Substances 0.000 abstract 1
- 229910002027 silica gel Inorganic materials 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 239000007921 spray Substances 0.000 abstract 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Molecular Biology (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1303724 Derivatives of the antibiotic wortmannin SANDOZ Ltd 27 April 1970 [14 May 1969 10 Sept 1969] 20182/70 Heading C2A The new fungistatic antibiotic 11-desacetoxywortmannin of Formula I may be prepared (a) by isomerizing #<SP>9(11)</SP>-8,9- dihydro - 1] - desacetoxy - wortmannin of Formula II or (b) by cultivating the S3196 strain of Penicillium funiculosum Thom preferably NRRL 3363, or the strain S8033/F of Aspergillus janus Raper and Thom, preferably NRRL 3807, or 11-desacetoxy-wortmannin producing mutants thereof in an aqueous nutrient medium containing assimilable carbon and nitrogen sources and inorganic salts, and isolating the resulting 11- desacetoxy-wortmannin. Preferably the isomerization is effected in an anhydrous organic base such as pyridine or quinolone under reflux in a nitrogen atmosphere and the product is recrystallized. In process (b) the antibiotic is isolated from the culture filtrate by extraction with ethyl acetate, benzene, chloroform, butyl acetate, methylene chloride or butanol, removal of solvent and optional chromatographic purification of the residue on e.g. alumina, silica gel or magnesium silicate, or by countercurrent distribution. #<SP>9(11)</SP> - 8,9 - Dihydro - 11 - desacetoxy - wortmannin is prepared by reacting wortmannin of Formula III under anhydrous conditions with zinc dust in an organic solvent in the presence of an acid. Pharmaceutical compositions having fungistatic, oedema- and inflammation-inhibiting effects comprise 11-desacetoxy-wortmannin and a pharmaceutical carrier or diluent. The compositions may be administered orally or topically in the form of powders, sprays, ointments, or tinctures.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH734969A CH520163A (en) | 1969-05-14 | 1969-05-14 | Novel steroid based antibiotic |
| CH1348569A CH523317A (en) | 1969-09-10 | 1969-09-10 | Novel steroid based antibiotic |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1303724A true GB1303724A (en) | 1973-01-17 |
Family
ID=25701168
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2018270A Expired GB1303724A (en) | 1969-05-14 | 1970-04-27 |
Country Status (8)
| Country | Link |
|---|---|
| AU (1) | AU1501370A (en) |
| BE (1) | BE750303A (en) |
| DE (1) | DE2022452A1 (en) |
| DK (1) | DK128006B (en) |
| FR (1) | FR2051522B1 (en) |
| GB (1) | GB1303724A (en) |
| IL (1) | IL34514A (en) |
| NL (1) | NL7006514A (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7049313B2 (en) | 2002-02-25 | 2006-05-23 | Kudos Pharmaceuticals Ltd. | ATM inhibitors |
| US7105518B2 (en) | 2001-08-14 | 2006-09-12 | Cancer Research Technology Limited | Thiopyrane-4-ones as DNA protein kinase inhibitors |
| US7226918B2 (en) | 2001-08-14 | 2007-06-05 | Cancer Research Technology Limited | DNA-PK inhibitors |
| US7402607B2 (en) | 2004-09-20 | 2008-07-22 | Kudos Pharmaceuticals Limited | DNA-PK inhibitors |
| US7429660B2 (en) | 2003-08-13 | 2008-09-30 | Kudos Pharmaceuticals Limited | ATM inhibitors |
| US7642254B2 (en) | 2005-02-09 | 2010-01-05 | Kudos Pharmaceuticals Limited | ATM inhibitors |
| US7696203B2 (en) | 2005-04-15 | 2010-04-13 | Kudos Pharmaceuticals Limited | DNA-PK inhibitors |
-
1970
- 1970-04-27 GB GB2018270A patent/GB1303724A/en not_active Expired
- 1970-05-04 NL NL7006514A patent/NL7006514A/xx unknown
- 1970-05-08 DE DE19702022452 patent/DE2022452A1/en active Pending
- 1970-05-12 FR FR707017286A patent/FR2051522B1/fr not_active Expired
- 1970-05-12 BE BE750303D patent/BE750303A/en unknown
- 1970-05-12 DK DK239770AA patent/DK128006B/en unknown
- 1970-05-13 AU AU15013/70A patent/AU1501370A/en not_active Expired
- 1970-05-13 IL IL34514A patent/IL34514A/en unknown
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7105518B2 (en) | 2001-08-14 | 2006-09-12 | Cancer Research Technology Limited | Thiopyrane-4-ones as DNA protein kinase inhibitors |
| US7226918B2 (en) | 2001-08-14 | 2007-06-05 | Cancer Research Technology Limited | DNA-PK inhibitors |
| US7674823B2 (en) | 2001-08-14 | 2010-03-09 | Cancer Research Technology Limited | DNA-PK inhibitors |
| US7049313B2 (en) | 2002-02-25 | 2006-05-23 | Kudos Pharmaceuticals Ltd. | ATM inhibitors |
| US7429660B2 (en) | 2003-08-13 | 2008-09-30 | Kudos Pharmaceuticals Limited | ATM inhibitors |
| US7402607B2 (en) | 2004-09-20 | 2008-07-22 | Kudos Pharmaceuticals Limited | DNA-PK inhibitors |
| US7732483B2 (en) | 2004-09-20 | 2010-06-08 | Kudos Pharmaceuticals Limited | DNA-PK inhibitors |
| US7642254B2 (en) | 2005-02-09 | 2010-01-05 | Kudos Pharmaceuticals Limited | ATM inhibitors |
| US7696203B2 (en) | 2005-04-15 | 2010-04-13 | Kudos Pharmaceuticals Limited | DNA-PK inhibitors |
Also Published As
| Publication number | Publication date |
|---|---|
| IL34514A (en) | 1974-01-14 |
| DE2022452A1 (en) | 1970-12-17 |
| NL7006514A (en) | 1970-11-17 |
| IL34514A0 (en) | 1970-07-19 |
| DK128006B (en) | 1974-02-18 |
| BE750303A (en) | 1970-11-12 |
| FR2051522A1 (en) | 1971-04-09 |
| FR2051522B1 (en) | 1973-08-10 |
| AU1501370A (en) | 1971-11-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PLNP | Patent lapsed through nonpayment of renewal fees |